I don’t think this is the right way to approach it tbh. You seem to have a lot of self-hatred, which is very common among gnc people, but try to work toward loving yourself as you are. There’s nothing wrong with being a cross dresser/wearing “women’s” clothing—I am the same but in the opposite direction. Not conforming to traditional masculinity does not make you broken or wrong; it’s society that’s wrong for placing such arbitrary expectations on sex. Once you 1) embrace your femininity and 2) realize that sex is essentially a meaningless but unchangeable part of who you are, like eye color or height, and doesn’t have to define you on any level beyond the superficial, you should feel a lot less pressure to transition. I did, at least.

I also suffer from ocd and have experienced similar thought processes. I can’t tell you what’s right for you, but for me, I feel like transitioning would have only made it worse. I would have become obsessed with feeling like I haven’t transitioned “enough” and kept trying new things and/or ended up totally dejected when I realized I’d treated my mental unease with permanent changes to my body. Think about the way you feel immediately after you do a compulsion and how long it takes before you feel like that compulsion wasn’t good enough and have to do it again. Now extrapolate that to hormonal treatments, surgeries, etc. For me, what helped the most was completely detaching gender roles from sex. My sex is unchangeable but that doesn’t mean it has to define me in any way beyond the obvious ones. Gender ideology places a lot of unnecessary baggage on manhood and womanhood and causes people who don’t fit neatly to become paranoid that there’s something wrong when it’s not us that’s wrong, it’s society.

If you want to, that’s your choice. But I’d urge you to think about what “being a woman” entails, to you. Is it having female hormones? Is it getting mistaken for a female in public? Or is it just embodying the social role expected of women? If it’s just the latter, you can easily do that as a man. And if the first two things are really important to you, are they important enough to you to go through the process and potential ramifications of medical transition, which causes health problems for many? If you really need people to “see you as a woman,” is it because you don’t feel like you can be liberated as yourself as a man? Ultimately, the only difference between medical transition and being a feminine man is the number of strangers on the street who will look at you and register you as a woman. And that seems more like a them-problem than a you-problem.

“Being a trans woman” is a pretty nebulous concept and one that every trans person seems to define it differently. Some think that no surgery/hormones are required at all. I guess you should determine whether superficial factors like breast growth are critical components of who you are. You won’t be a different person on the inside if you have boobs. Sex is superficial. But for some people, physical alterations to their bodies makes them feel more comfortable—lots of cis women get breast augmentations/reductions because it helps their confidence and I don’t think they’re necessarily wrong for that, but it’s still the case that they’ve tied up some essential essence of “who they are” in a superficial trait. I’ve also found, personally, that when I fixate more on parts I’m dysphoric about, I get more dysphoric because they’re not “perfect.” I used to bind, and it always made me uncomfortable because I felt like just the fact of having to bind was a reminder of the fact that I wouldn’t be male (I also think that in my case this is highly linked to my ocd, but OCD has over a 6x prevalence in gender dysphoric individuals compared to the general population, so they’re likely related. And I always encourage people to make sure they DONT have ocd if they decide to transition because OCD by the nature of how it functions will never be satisfied by any amount of “transition”).

I’ve had the exact same thing (also have OCD) and didn’t start transitioning bc I knew it was an obsession. I identified as nb briefly and it made the obsessive thoughts/dysphoria worse bc I became even more preoccupied with it and started checking strangers’ faces on the street when I walked by to see if I could determine whether they “perceived” me correctly and that’s when I knew transition wasn’t for me. Doing marginally better since I just committed myself to living and presenting as I want, accepting my bio sex for what it is, and not getting wrapped up in the gender stuff. Good luck my friend. OCD is a mindfuck